Triethylamine → HCID 67605974, compound

HRID 1619550Notes

Reaction equation

HRID 1619550 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:6].C(N(CC)CC)C.[F:29][C:30]1[CH:31]=[C:32]([S:37](Cl)(=[O:39])=[O:38])[CH:33]=[CH:34][C:35]=1[F:36]>C(Cl)Cl>[F:29][C:30]1[CH:31]=[C:32]([S:37]([NH:3][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]([O:7][C@@H:8]2[CH:13]3[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]3)[CH2:9]2)=[O:6])(=[O:38])=[O:39])[CH:33]=[CH:34][C:35]=1[F:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27369133,4-Difluorobenzene-1-sulfonyl chlorideHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67605974HCID 67605974, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (110 mg, 0.33 mmol) was suspended in DCM (4 ml), and triethylamine (121 μl, 1.65 mmol) was added obtaining a solution. 3,4-difluorobenzene-1-sulfonyl chloride (53.1 μl, 0.40 mmol) was added, and the reaction was stirred at RT for 3 hours. The reaction was diluted with DCM and washed with water and brine. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The residue was triturated with Et2O to obtain (R)-quinuclidin-3-yl 2-(3,4-difluorophenylsulfonamido)-2-phenylacetate (40 mg; 28% yield), which was used as such in the next step.

Workup

  1. customobtaining a solution
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-88357eafb4494b2c9add3dc207f75038
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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